Cyanoacetamide → alpha-Cyano-beta-(2-Nitro-5-Fluorophenyl)Acrylamide

HRID 2163577Notes

Reaction equation

HRID 2163577 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)[CH:5]=O.[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14].N1CCCCC1>C(O)C>[C:13]([C:15](=[CH:5][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:7]=1[N+:10]([O-:12])=[O:11])[C:16]([NH2:18])=[O:17])#[N:14]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 5870905-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 53864188alpha-Cyano-beta-(2-Nitro-5-Fluorophenyl)Acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-fluoro-6-nitrobenzaldehyde (10.0 g., 0.0592 mole), 2-cyanoacetamide (5.24 g., 0.0622 mole), piperidine (0.37 g., 4.36 millimole) and ethanol (92 ml.) is heated to reflux on a steam bath for two hours. It is then cooled in an ice-bath whereupon the product precipitates and is recovered by filtration, washed with cold ethanol and dried. Yield = 9.1 g. (65%) of crude product. M.P. 162°-166° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux on a steam bath for two hours
  3. temperatureIt is then cooled in an ice-bath whereupon the product
  4. customprecipitates
  5. filtrationis recovered by filtration
  6. washwashed with cold ethanol
  7. customdried

Sources & evidence

ORD record
ord-632e27a1b3a84faf9145ca43a155e810
Source dataset
uspto-grants-1979_01
Patent number
US04134981

Reaction notes

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